Tetrahydrofuran → 2-Methyl-N-(oxetan-3-ylidene)propane-2-sulfinamide

HRID 624272

Reaktionsgleichung

Reaktionsgleichung von HRID 624272
[CH3:1][C:2]([S:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[O:8]1[CH2:12][CH2:11][CH2:10]C1.O1CC(=O)C1>[Cl-].[Na+].O.C(O[Ti](OCC)(OCC)OCC)C>[CH3:1][C:2]([S:5]([N:7]=[C:11]1[CH2:10][O:8][CH2:12]1)=[O:6])([CH3:4])[CH3:3]

Komponenten

6

Edukt 3

HCID 8028TetrahydrofuranHCID 3382465Tert-ButanesulfinamideHCID 150242543-Oxetanone

Produkt 1

HCID 468399952-Methyl-N-(oxetan-3-ylidene)propane-2-sulfinamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178477244HCID 178477244, VerbindungKatalysatorHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a 250 mL round-bottomed flask was added 2-methylpropane-2-sulfinamide (3.36 g, 27.8 mmol) followed by tetraethoxytitanium (11.64 ml, 55.5 mmol) to a tetrahydrofuran (69.4 ml) solution of oxetan-3-one (2 g, 27.8 mmol) at room temperature. The mixture was stirred at 50° C. for 5 hours, cooled and poured into brine. The suspension was filtered through a pad of diatomaceous earth eluting with ethyl acetate. The organics were combined, dried with sodium sulfate, filtered and concentrated under vacuum. The residue was purified by regular phase flash column chromatography to give the title compound.

Aufarbeitung

  1. temperaturecooled
  2. filtrationThe suspension was filtered through a pad of diatomaceous earth
  3. washeluting with ethyl acetate
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by regular phase flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3d453ee755554741a9d6bc4cb6c12527
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09302989B2

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